Most companies don’t reach maturity until they hit the 5–7-year mark. Many of these companies are still figuring out whom they will become. This can most clearly be seen internally as it most commonly shows up in the employee experience. However, externally, with customers and other key stakeholders may not be so clear from the beginning. Influential leaders wait until the last moment to cement behaviors as it becomes difficult to change the culture.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Reginald L. James.

From all-too-familiar hiring heartaches of tech scaleups to the pure joy of landing that right person, Reggie James has experienced it all. He is the host of the upcoming Sprint Hard, Iterate Fast Podcast, a startup founder, author of ScaleUp Culture: How to Scale your Teams Without Killing your Culture, and CEO of Beaker & Flint, a digital product resource consultancy based in Melbourne, Australia.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

I previously had two business partners, and collectively we ran a consultancy that did agile transformation, product innovation, and fundraising innovation. Those partners are exiting the business, and I’ve decided to scale the business back to serve our scale-up clients. Our new offering will be a contract recruitment service helping innovative tech companies to build their product and software delivery teams. Our primary branding and business development vehicle will be a podcast called Sprint Hard, Iterate Fast. I’ll speak with CEOs, CTOs, and Product Leaders about product, team, and culture topics. These new projects have been fascinating.

Additionally, I’m soon to release a book entitled ScaleUp Culture. The book is for new CEOs, entrepreneurs, and Leaders of scaling technology businesses. It compiles my lessons in scaling teams and warns CEOs not to neglect company culture while scaling.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

The most influential leader in my life was an Elder in the church I grew up attending. His name is Bill Throne. I’d once heard a story about him that changed me forever. A retired navy pilot, he needed to find some profession that would take care of his family. He spent three years living off credit cards with three children to pivot his career into commercial real estate sales. He paid off all his debts with his first significant sale. He went on to do very well in his career, even to the point of capping his income because he was making so much money.

I learned two valuable lessons from Bill. The first was faith. Bill had tremendous confidence in himself and clearly in something bigger than himself. It led him to take calculated risks, and he won big. The second lesson was being incorruptible. Money and power can knock many people off course, and bill gave much of his wealth away to guard his heart against greed and corruption. His example leads me to prioritize what’s essential while being calculated in my risk-taking.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

My biggest mistake was attempting to scale a consulting business that hadn’t reached a product-market fit. I hired some heavy-weight sales capability on to find out that our services were difficult to sell and would be difficult to scale. Consulting businesses are already notoriously difficult to scale because there isn’t any underlying product that can be built once and sold repeatedly. In consulting, we’re just selling time. What ended up happening is that all of the added effort burned our team out. I discovered that a profitable small business is better than a large unprofitable one. There are cases where this isn’t true. Many large tech companies never make a profit yet still have astronomic valuations. But in the case of small to medium-sized professional services businesses, profit is better.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

I used to think a lot about leadership. I once read many books on leadership. I’ve always believed that every organization needs good leadership — someone who understands people, knows how to relate to them, talks to them, finds their passions and speaks in a way that energizes them. Today my view of leadership is very different. Those things are essential, but organizations must adapt to change quickly. The average time employees stay in a company steadily decreases, requiring leaders to create happy and productive environments to see an ROI on a new hire. Today, leadership is less about influencing a few people to drive an outcome. Today, it’s much more about fostering the right environment and creating the space for productivity and creativity.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

I’ve stopped caring so much. It bothered me if my employees were unhappy or less than satisfied with our workplace. We did quarterly surveys, and I paid so much attention to those results. I studied them. I tried to analyze the results and understand people’s responses. Our results were consistently higher than the industry standard, yet I still obsessed over them. I discovered there is such a thing as caring too much. Today, rather than being hyperaware of the company culture or my leadership, I focus more on playing to my strengths and leaning into my natural disposition. I’m a lot like my dad — we present a hard exterior — that people may often perceive as “scary.” The other benefit of that natural disposition is that people tend to work harder or put more effort into their work. I’ve stopped thinking of this as a “bug” within my character and just accepted that’s the way it is.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

I’ve started cultivating the discipline of focus. As an entrepreneur, I’m excited about lots of new shiny ideas. Every week I have new ideas or am pitched new business ideas that I’ve learned to say no to. I think all leaders need to master the art of focus.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

Perhaps it’s cliché, but people say we must continue to learn — it’s so true. And sometimes learning (or possibly unlearning) can be painful. It’s comfortable being able to rely on our old knowledge or the skills and traits that helped us to succeed. But the world is changing rapidly. If we don’t continue to learn — and I mean to learn through doing, we will fall behind.

Many readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

My advice for new and emerging leaders is to ‘know thyself.’ You cannot lead other people if you scarcely know yourself. And knowing yourself is more complicated than you think. If you aren’t spending at least six to ten hours a week alone, thinking, praying, or meditating, it’s easy to get out of sync with yourself. Stay out of sync long enough, and you’ll lose sight of who you are. Doing so is the equivalent of the blind leading the blind. Get a coach. Get a mentor. Heck, get a psychologist. Do the work to reflect on who you are; it’ll provide you with the priceless clarity you need to lead others.

Based on your experience or research, what are the top five traits effective leaders exemplify now?

They get to know whom the organization needs to become before codifying values and behaviors.

Most companies don’t reach maturity until they hit the 5–7-year mark. Many of these companies are still figuring out whom they will become. This can most clearly be seen internally as it most commonly shows up in the employee experience. However, externally, with customers and other key stakeholders may not be so clear from the beginning. Influential leaders wait until the last moment to cement behaviors as it becomes difficult to change the culture.

They never copy the leadership and culture development strategies of other well-known companies.

The Netflix employee handbook became extremely famous on SlideShare, a website allowing users to share presentations. The employee handbook stated no maximum number of days an employee could take off. In addition, employees were not required to seek approval for days off. At the time, these practices were uncommon. I’ve witnessed many companies copy the practices described in Netflix’s cultural handbook, leading to detrimental effects. This is because Netflix’s mission, people, goals, and collective view of the world are vastly different from any other company. The culture set by Reed Hastings is admirable but not replicable. Most companies do not have a psychologically safe, supportive, or responsible culture to have an unlimited leave policy. Businesses that try to replicate this employee benefit often experience adverse effects. Implementing this policy often leads to a worse work-life balance, where employees take less time off than before.

They develop and deliver a compelling vision that excites

Scott Bateman, a past client, and a visionary executive in a Melbourne, Australia-based property management company, saw an unprecedented opportunity to transform the industry when a billionaire entrepreneur purchased a real estate firm developing a property management tool. Despite its past success, the tool had fallen out of use and the property management sector in Australia had not seen any innovation in over 50 years. This focus on cost-cutting for owners resulted in a challenging experience for renters, owners, and property managers, with issues like scheduling conflicts and owner approval delays causing widespread frustration.

Scott’s vision for Kolmeo, Dutch for “triangle,” was game-changing. He saw that the key to unlocking value and reinventing the property management profession in Australia lies in improving relationships between renters, owners, and property managers. This vision was so impactful that after presenting the prototype to the board, he secured $14 million in funding to bring Kolmeo to life. The team then started building Kolmeo’s team with contractors eager to join, driven by Scott’s electric story and vision for the industry’s future. Scott’s vision for Kolmeo was paramount, as it had the power to revolutionize the property management sector in Australia.

They focus on the minimum viable culture to reach key milestones.

Leaders in new and scaling businesses should create a culture that marginally outpaces the acceptable limits of what’s required to attract and retain the best people in the company successfully. This approach is pragmatic and cost-effective, and it won’t lead to perfect company culture and is unlikely to deserve a “best place to work” award, but it gives the founding team precious time to hit key funding milestones. The leadership approach acknowledges that the culture won’t be perfect and that people may choose to leave as a result.

They are involved in every interview

Larry Page of Google was famously involved in the interview process of all Googlers. Google had 53,600 full-time employees at the start of 2015, compared to 47,800 the year before. In one year, the company hired about 6,000 new people. According to Google HR boss Laszlo Bock, who writes about Google’s hiring process in his book Work Rules!, cofounder and CEO Larry Page approved each of them.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

Every day is like a brushstroke onto the canvas that is our lives. It’s really about putting our best effort into every single day. I could say that I embody that quote regularly. Some days are more like doodles on a page. Particularly as I transition from shutting down one business to beginning a new one, those doodles are the sketches of a new vision — a new future. I’d like to believe those days that feel like doodles are simply the outlines on the following drawing that will become the masterpiece. Every day isn’t a mountain top day; most days are spent climbing.

What is the legacy you aspire to leave as a leader?

I began my leadership journey wanting to do more and be more than I ever thought possible. Life has a funny way of making your achievements and successes feel normal. My legacy will be my relentless pursuit of growth and progress as a person. I’ve always believed that if I was comfortable, I was doing something wrong. I think that will be my legacy. The willingness to push beyond the boundaries that were set from birth. The limits that were thrust upon us from our community or our heritage. My legacy will be my tenacity to shoot for the stars. If I miss and hit the moon, that’ll be just fine.

How can our readers connect with you to continue the conversation?

They can reach out on linkedin or e-mail me directly at [email protected]

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!